Trifluoroacetic acid → 5-[(R)-3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid ethyl ester

HRID 1253906Notes

Reaction equation

HRID 1253906 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:15]=1[CH2:14][N:13]([C:16](=[O:37])[CH2:17][C@H:18]([NH:29]C(OC(C)(C)C)=O)[CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=1[F:28])[CH2:12][C:11]1[CH:38]=[CH:39][CH:40]=[CH:41][C:10]2=1)=[O:5])[CH3:2].[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>C(Cl)Cl>[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45].[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][N:9]2[C:15]=1[CH2:14][N:13]([C:16](=[O:37])[CH2:17][C@H:18]([NH2:29])[CH2:19][C:20]1[CH:25]=[C:24]([F:26])[C:23]([F:27])=[CH:22][C:21]=1[F:28])[CH2:12][C:11]1[CH:38]=[CH:39][CH:40]=[CH:41][C:10]2=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 68776113(R)-5-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-5,6-dihydro-4H-2,5,10b triaza-benzo[e]azulene-3-carboxylic acid ethyl ester

Product 2

HCID 6422Trifluoroacetic acidHCID 441556695-[(R)-3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid ethyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (R)-5-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-5,6-dihydro-4H-2,5,10b triaza-benzo[e]azulene-3-carboxylic acid ethyl ester (100 mg, 0.174 mmol) in DCM (5 mL), was added trifluoroacetic acid (0.52 mL, 3 mL/mmol). The reaction mixture was stirred at r.t. for 1 h. After completion of the reaction, as confirmed by TLC, excess of trifluoroacetic acid and DCM were evaporated in vacuo to afford a gummy solid which was crystallised from hexane to afford trifluoroacetic acid salt of 5-[(R)-3-amino-4-(2,4,5-trifluoro-phenyl)-butyryl]-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid ethyl ester (80 mg, 79%).

Workup

  1. customAfter completion of the reaction
  2. customwere evaporated in vacuo
  3. customto afford a gummy solid which
  4. customwas crystallised from hexane

Sources & evidence

ORD record
ord-43e23a9bf7994a5ab4a8673ec333f350
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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